1-Chloroethyl chloroformate → HCID 68291683, compound

HRID 877694Notes

Reaction equation

HRID 877694 reaction equation
C([N:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[C@H:10]([CH2:23][CH3:24])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[CH2:23]([C@H:10]1[C@H:11]([NH:14][C@H:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH3:16])[CH2:12][CH2:13][NH:8][CH2:9]1)[CH3:24]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 68350377HCID 68350377, compound

Product 1

HCID 68291683HCID 68291683, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (3R,4R)-1-benzyl-3-ethyl-N—((S)-1-phenylethyl)piperidin-4-amine (679.2 mg, 2.106 mmol) in 1,2-dichloroethane (3.50 ml) at 0° C. was added 1-chloroethyl chloroformate (0.276 ml, 2.53 mmol) dropwise. After stirring for 20 minutes, the ice-bath was removed and the reaction was heated to reflux for 1 hr. The reaction was cooled to room temperature and concentrated under reduced pressure. Methanol (10.5 ml) was added, and the reaction was heated to reflux for 2 hrs. After removal of the solvent, the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated under reduced pressure, yielding (3R,4R)-3-ethyl-N—((S)-1-phenylethyl)piperidin-4-amine (443 mg, 1.906 mmol, 91.0% yield) as a yellow oil. LCMS (Method K) m/z 233.3 ([M+H]+).

Workup

  1. customthe ice-bath was removed
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 1 hr
  4. concentrationconcentrated under reduced pressure
  5. additionMethanol (10.5 ml) was added
  6. temperaturethe reaction was heated
  7. temperatureto reflux for 2 hrs
  8. customAfter removal of the solvent
  9. customthe residue was partitioned between ethyl acetate and water
  10. washThe organic layer was washed with brine
  11. dry with materialdried with sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0323c7dd11e546baa93bd27673497f33
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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